Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[(2-hydroxy-5-methylbenzylidene)amino]benzonitrile

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Faizi M. S. H., Cinar E. B., Aydin A. S., Ağar E., DEGE N., Mashrai A.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.76, ss.1195-1204, 2020 (ESCI) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 76
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1107/s2056989020008907
  • Dergi Adı: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus
  • Sayfa Sayıları: ss.1195-1204
  • Anahtar Kelimeler: crystal structure, 2-hydroxy-5-methyl-benzaldehyde, 2 aminobenzonitrile, Schiff base, COMPLEXES, IMINES
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

The title compound, C15H12N2O, was synthesized by condensation reaction of 2-hydroxy-5-methylbenzaldehyde and 2-aminobenzonitrile, and crystallizes in the orthorhombic space group Pbca. The phenol ring is inclined to the benzonitrile ring by 25.65 (3)degrees. The configuration about the C=N bond is E, stabilized by a strong intramolecular O-H center dot center dot center dot N hydrogen bond that forms an S(6) ring motif. In the crystal, C-H center dot center dot center dot O and C-H center dot center dot center dot N interactions lead to the formation of sheets perpendicular to the a axis. C-H center dot center dot center dot pi interactions, forming polymeric chains along the a-axis direction, connect these sheets into a threedimensional network. A Hirshfeld surface analysis indicates that the most important contributions for the packing arrangement are from H center dot center dot center dot H and C center dot center dot center dot H/H center dot center dot center dot C interactions. The density functional theory (DFT) optimized structure at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined molecular structure and the HOMO-LUMO energy gap is given.